RESUMO
The aim of this study was to investigate the antibacterial activity of red propolis and resin and their association with standard antibiotics to evaluate possible differences of activity. We also submitted red propolis and the resin to a HPLC analysis to confirm the botanical origin. The extracts were tested against P. aeruginosa and S. aureus alone and in association with gentamicin and imipenem. The HPLC analysis identified seven compounds with six of them present in both substances. The lowest MIC values obtained in this study were observed against S. aureus. In general, MIC values showed to be lower for red propolis against all species tested in comparison to resin. Despite the synergistic behavior to be similar for both substances, we observed that inhibitory concentrations of drugs were lower when associated with red propolis in comparison to resin.
Assuntos
Antibacterianos/farmacologia , Dalbergia/química , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Própole/farmacologia , Resinas Vegetais/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Brasil , Cromatografia Líquida de Alta Pressão , Avaliação Pré-Clínica de Medicamentos , Testes de Sensibilidade Microbiana , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Própole/química , Própole/isolamento & purificação , Resinas Vegetais/química , Resinas Vegetais/isolamento & purificação , Staphylococcus aureus/efeitos dos fármacosRESUMO
Ipomoea tyrianthina Lindley (syn. I. orizabensis Pelletan, Lebed. ex Steud., Convolvulaceae) is known as a purgative, but it has been also used in Mexican traditional medicine in the treatment of seizures and pain for their anticonvulsive, hypnotic and sedative properties. Some glycolipids isolated from this plant have shown significant effects on Central Nervous System, modifying inhibitory or excitatory processes. The mechanism for such activity it is not clear; studies with these metabolites have suggested that a pore-forming mechanism is involved in their activity. Therefore, the present work explores a possible not pore-forming mechanism related to the effect of four resin glycosides, Scammonin 1 (S-1), tyrianthin C (T-C), tyrianthin A (T-A) and tyrianthinic acid VI (TA-VI), isolated from Ipomoea tyrianthina root on GABAergic transmission system in cerebral cortex slices of mouse brain in an in vitro model. The results obtained show that all glycolipids tested evoked endogenous GABA release and increased its concentration within the incubation medium compared with controls; T-C demonstrated a dose-dependent effect. Sodium absence and guvacine presence did not affect significantly the activity of S-1 and T-C in contrast to T-A and TA-VI. S-1 and T-C effects were calcium-dependent, where GABA concentrations were considerably reduced. These results suggest that the increase of endogenous γ-aminobutyric acid (GABA) released evoked by these glycolipids is possibly done through a Na+- and/or Ca2+-dependent mechanisms, discarding a pore-forming mechanism.
Assuntos
Cálcio/metabolismo , Glicosídeos/farmacologia , Ipomoea , Resinas Vegetais/farmacologia , Sódio/metabolismo , Ácido gama-Aminobutírico/metabolismo , Animais , Córtex Cerebral/efeitos dos fármacos , Córtex Cerebral/metabolismo , Relação Dose-Resposta a Droga , Camundongos , Técnicas de Cultura de Órgãos , Raízes de Plantas , Resinas Vegetais/isolamento & purificaçãoRESUMO
CONTEXT: The resin from the trunk wood of Virola oleifera (Schott) A. C. Smith (Myristicaceae) is used in folk medicine to hasten wound repair and to treat pain and inflammatory conditions, and our previous report indicated the anti-oxidative properties in other oxidative stress model. OBJECTIVE: To investigate the protective effects of resin from V. oleifera in two experimental models of gastric ulcer oxidative-stress dependent. MATERIALS AND METHODS: Plant material was collected and the resin was subjected to partitioning with organic solvents. The buthanol fraction was subjected to chromatographic and spectrometric methods for isolation and structural elucidation. The resin was quantified for polyphenols and flavonoids by colorimetric methods. Furthermore, the antioxidant activity of resin was determined by three different methods. The ulcers were induced acutely in Swiss male mice with ethanol/HCl and indomethacin using single-doses of 10 and 100 mg/kg. The gastroprotection of the experimental groups was comparable to reference control lansoprazole (3 mg/kg). RESULTS: The high content of polyphenols (â¼82%) and the presence of epicatechin and eriodictyol were determined. The LD50 was estimated at 2500 mg/kg. At minimum (10 mg/kg) and maximum (100 mg/kg) dosage of resin, both in ethanol/HCl as indomethacin ulcer induction models demonstrate reduction of lesions (minimum: â¼97% and â¼66%; maximum: â¼95% and â¼59%). DISCUSSION: The gastroprotection might be related to tannins, phenolic acids and flavonoids present in the resin by antioxidant properties. CONCLUSIONS: The results indicate that this resin has gastroprotective activity probably associated with the presence of phenolic antioxidant substances.
Assuntos
Antioxidantes/farmacologia , Mucosa Gástrica/efeitos dos fármacos , Myristicaceae/química , Extratos Vegetais/farmacologia , Resinas Vegetais/farmacologia , Úlcera Gástrica/prevenção & controle , Animais , Antiulcerosos/química , Antiulcerosos/isolamento & purificação , Antiulcerosos/farmacologia , Antiulcerosos/toxicidade , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/toxicidade , Benzotiazóis/química , Cromatografia em Camada Fina , Modelos Animais de Doenças , Etanol , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Mucosa Gástrica/patologia , Ácido Clorídrico , Indometacina , Dose Letal Mediana , Masculino , Camundongos , Fitoterapia , Casca de Planta , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Plantas Medicinais , Polifenóis/isolamento & purificação , Polifenóis/farmacologia , Resinas Vegetais/química , Resinas Vegetais/isolamento & purificação , Resinas Vegetais/toxicidade , Solventes/química , Espectrometria de Massas por Ionização por Electrospray , Úlcera Gástrica/induzido quimicamente , Úlcera Gástrica/patologia , Ácidos Sulfônicos/química , Espectrometria de Massas em TandemRESUMO
Recycling liquid chromatography was used for the isolation and purification of resin glycosides from the CHCl3-soluble extracts prepared using flowers of Ipomoea wolcottiana Rose var. wolcottiana. Bioassay-guided fractionation, using modulation of both antibiotic activity against multidrug-resistant strains of Gram-negative bacteria and vinblastine susceptibility in breast carcinoma cells, was used to isolate the active glycolipids as modulators of the multidrug resistance phenotype. An ester-type dimer, wolcottine I, one tetra- and three pentasaccharides, wolcottinosides I-IV, in addition to the known intrapilosin VII, were characterized by NMR spectroscopy and mass spectrometry. In vitro assays established that none of these metabolites displayed antibacterial activity (MIC>512 µg/mL) against multidrug-resistant strains of Escherichia coli, and two nosocomial pathogens: Salmonella enterica serovar Typhi and Shigella flexneri; however, when tested (25 µg/mL) in combination with tetracycline, kanamycin or chloramphenicol, they exerted a potentiation effect of the antibiotic susceptibility up to eightfold (64 µg/mL from 512 µg/mL). It was also determined that these non-cytotoxic (CI50>8.68 µM) agents modulated vinblastine susceptibility at 25 µg/mL in MFC-7/Vin(+) cells with a reversal factor (RFMCF-7/Vin(+)) of 2-130 fold.
Assuntos
Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Resistência a Múltiplos Medicamentos/efeitos dos fármacos , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Ipomoea/química , Resinas Vegetais/isolamento & purificação , Resinas Vegetais/farmacologia , Antibacterianos/química , Escherichia coli/efeitos dos fármacos , Feminino , Flores/química , Glicosídeos/química , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Resinas Vegetais/química , Salmonella/efeitos dos fármacos , Vimblastina/farmacologiaRESUMO
OBJECTIVES: The hormonal treatment for endometriosis frequently fails to completely eradicate endometriotic implants. A new therapeutic treatment is needed. This study investigates the in-vitro effect of Copaifera langsdorffii oil-resin on human eutopic and ectopic endometrium stromal cell cultures (EuESCs and EctESCs). METHODS: A nanocomposite system containing the copaiba oil-resin (NanoCOR) was developed and acute toxicity test was performed. Endometrial stromal cells (ESCs) from non-endometriotics controls (CESCs), EuESCs and EctESCs were isolated and treated with different concentrations of NanoCOR, at different time intervals to evaluate its effect on cell morphology, proliferation, viability, necrosis and apoptosis induction. KEY FINDINGS: When treated with 50 µg/ml of NanoCOR, the morphology of EctESCs changed, as the actin microfilaments were disorganized, disassembled or disrupted. Moreover, at 24 h of treatment with NanoCOR, the EctESCs viability was inhibited, and a significant number of these cells underwent apoptosis. In EuESCs, these effects were observed only at 48 h. Finally, the treatment of EctESCs with NanoCOR increased the lactate dehydrogenase release into the extracellular medium more than in EuESCs. CONCLUSIONS: Our data indicate that NanoCOR has a greater impact on the behaviour of human endometriotic stromal cells than on the eutopic endometrium stromal cells, supporting the idea that NanoCOR should be further investigated as a novel and valuable alternative to treat endometriosis.
Assuntos
Forma Celular/efeitos dos fármacos , Endometriose/tratamento farmacológico , Endométrio/efeitos dos fármacos , Fabaceae/química , Óleos de Plantas/farmacologia , Resinas Vegetais/farmacologia , Células Estromais/efeitos dos fármacos , Árvores , Citoesqueleto de Actina/efeitos dos fármacos , Citoesqueleto de Actina/patologia , Animais , Apoptose/efeitos dos fármacos , Estudos de Casos e Controles , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Células Cultivadas , Relação Dose-Resposta a Droga , Endometriose/patologia , Endométrio/patologia , Feminino , Humanos , Masculino , Camundongos , Nanopartículas , Necrose , Fitoterapia , Óleos de Plantas/isolamento & purificação , Óleos de Plantas/toxicidade , Plantas Medicinais , Floresta Úmida , Resinas Vegetais/isolamento & purificação , Resinas Vegetais/toxicidade , Células Estromais/patologia , Fatores de Tempo , Clima TropicalRESUMO
Este trabalho teve como objetivo o mapeamento da composição do óleo essencial (OE) de Corymbia citriodora produzido no Brasil pelas principais destilarias, Três Barras (FTB) e Meneghetti (FMG), e a extração do OE e oleoresina (OR) a partir das folhas utilizando a tecnologia de fluidos supercríticos. Foram estudados os efeitos das condições do processo, pressão (P) e temperatura (T), sobre a composição química e rendimento dos extratos, além da atividade antioxidante de alguns ensaios. As folhas picotadas apresentaram umidade de 7,33±1,1 e 8,66±0,5% para a FMG e FTB, respectivamente. As extrações, a partir das folhas com CO2 em condições sub e supercríticas, foram realizadas em duas etapas. Na primeira etapa, obteve-se o OE e, em seguida, as condições foram reajustadas para se fazer a extração da OR. As combinações das variáveis P e T foram determinadas conforme um delineamento composto central rotacional (DCCR), sendo feito um para cada etapa de extração. Para todos os extratos obtidos na primeira etapa, bem como dos OEs obtidos por arraste à vapor (AV) e hidrodestilação (HD), determinou-se o perfil de voláteis por cromatografia gasosa acoplado ao espectrofotômetro de massa (GC/MS). Os ensaios de maior rendimento em OE sem a coextração de pigmentos (100 bar e 60ºC, FTB=1,59% e FMG= 1,56%) e OR (220 bar e 70ºC, FTB=1,59% e FMG= 1,56%) tiveram sua atividade antioxidante determinada pelos métodos DPPH e branqueamento do β-caroteno. [...] Os resultados encontrados demonstram que através das condições adequadas de extração com CO2 supercrítico é possível a obtenção de um OE enriquecido em citronelal e de uma OR com alta atividade biológica. A técnica também permite um melhor aproveitamento da matéria-prima, através da extração sequencial e seletiva de OE e OR, em relação aos métodos convencionais.
The aim of this work was to evaluate the Corymbia citriodora essential oil (EO) composition produced by the main Brazilian distilleries; Meneghetti and Três Barras moreover evaluate the yield, composition and biological activity of (EO) and oleoresin (OR) obtained from leaves by using supercritical fluids technology. The effects of operational conditions, pressure (P) and temperature (T), on chemical composition and yield were studied. The cut leaves showed moisture content of 7,33±1,1 and 8,66±0,5% to FMG and FTB samples, respectively. The extractions using CO2 in sub and supercritical conditions were performed in two steps. In the first step the EO was obtained. After, the operational conditions were readjusted to make the OR extraction. The P and T values were determined using a complete factorial experimental design (CFED). It was used two experimental designs, one for each step. The volatile profile of all EO, obtained by steam distillation (AV), hydrodistillation (HD) and SFE were determined using a gas chromatography coupled with mass spectrometer (GC/MS) equipment. The experiments that provide the higher yields in EO without pigments coextraction (100 bar e 60ºC, FTB=1,59% e FMG= 1,56%) and OR (220 bar e 70ºC, FTB=1,59% e FMG= 1,56%) had their antioxidant activity determined by DPPH test and β-carotene bleaching assay. The OR was also evaluated for its content of total flavonoids and total phenolics by two different methods, Prussian Blue and Folin-Ciocalteu. [...] The results obtained suggest that by using the SFE it is possible to obtain an EO with a high citronellal concentration. OR also showed a high antioxidant capacity. The SFE technique also improve the raw material utilization by the sequencial and selective extraction of EO and OR, in relation of conventional methods.
Assuntos
Cromatografia com Fluido Supercrítico , Eucalyptus/química , Resinas Vegetais/isolamento & purificação , Óleos Voláteis/isolamento & purificação , Dióxido de Carbono/administração & dosagem , Exploração de Recursos Naturais/métodosRESUMO
Seventeen diterpenes belonging to the labdane, abietane and isopimarane skeleton classes were isolated from the resin of the Chilean gymnosperm Austrocedrus chilensis and identified by spectroscopic and spectrometric methods. The diterpene 12-oxo-labda-8(17),13E-dien-19 oic acid is reported for the first time as a natural product and 14 diterpenes are reported for the first time for the species.
Assuntos
Cupressaceae/química , Diterpenos/isolamento & purificação , Resinas Vegetais/isolamento & purificação , Cromatografia Gasosa , Diterpenos/química , Espectroscopia de Ressonância Magnética , Resinas Vegetais/químicaRESUMO
A reinvestigation of the CHCl 3-soluble extract from flowers of the Mexican medicinal arborescent morning glory, Ipomoea murucoides, through preparative-scale recycling HPLC, yielded six new pentasaccharides, murucoidins VI-XI (1- 6), as well as the known pescaprein III (7), stoloniferin I (8), and murucoidins I-V (9- 13). Their structures were characterized through the interpretation of their NMR spectroscopic and FABMS data. Compounds 1-6 were found to be macrolactones of three known glycosidic acids identified as simonic acids A and B, and operculinic acid A, with different fatty acids esterifying the same positions, C-2 on the second rhamnose unit and C-4 on the third rhamnose moiety. The lactonization site of the aglycone was placed at C-2 or C-3 of the second saccharide unit. The esterifying residues were composed of two short-chain fatty acids, 2-methylpropanoic and (2S)-methylbutyric acids, and two long-chain fatty acids, n-dodecanoic (lauric) acid and the new (8R)-(-)-8-hydroxydodecanoic acid. For the latter residue, its absolute configuration was determined by analysis of its Mosher ester derivatives. All members of the murucoidin series exerted a potentiation effect of norfloxacin against the NorA overexpressing Staphylococcus aureus strain SA-1199B by increasing the activity 4-fold (8 microg/mL from 32 microg/mL) at concentrations of 5-25 microg/mL. Stoloniferin I (8) enhanced norfloxacin activity 8-fold when incorporated at a concentration of 5 microg/mL. Therefore, this type of amphipathic oligosaccharide could be developed further to provide more potent inhibitors of this multidrug efflux pump.
Assuntos
Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Farmacorresistência Bacteriana Múltipla , Ácidos Graxos/isolamento & purificação , Glicosídeos/isolamento & purificação , Ipomoea/química , Proteínas de Membrana Transportadoras/metabolismo , Plantas Medicinais/química , Resinas Vegetais/isolamento & purificação , Staphylococcus aureus/efeitos dos fármacos , Antibacterianos/química , Sequência de Carboidratos , Cromatografia Líquida de Alta Pressão , Ácidos Graxos/química , Glicosídeos/química , Proteínas de Membrana Transportadoras/efeitos dos fármacos , México , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Resinas Vegetais/química , Staphylococcus aureus/genética , Staphylococcus aureus/metabolismoRESUMO
Ipomoea pes-caprae (beach morning-glory; "riñonina" for the herbal drug in Mexico) is prescribed by traditional healers to moderate "heat" in an infected kidney. The hexane-soluble extract from the aerial parts of this medicinal plant, through preparative-scale recycling HPLC, yielded six new lipophilic oligosaccharides of jalapinolic acid: pescaproside B (1) and pescapreins V-IX (2-6). The previously known pescaproside A (7), pescapreins I-IV (8-11), and stoloniferin III (12) were also identified in the analyzed material by means of HPLC comparison with authentic samples. The glycosidic acid structure for all pentasaccharides was confirmed as simonic acid B. Pescaproside B (1), an acylated glycosidic acid methyl ester, is structurally related to pescaprein III (10). Pescapreins V (2) and VI (3) are diasteroisomeric tetraglycosidic lactones of operculinic acid C. Both of these compounds contain (2S)-methylbutyric and n-dodecanoic acids as their esterifying residues. Pescapreins VII (4) and IX (6) are pentasaccharides that contain an n-decanoyl group as their esterifying fatty acid residue instead of the n-dodecanoyl found in pescapreins I (8) and IV (11). Pescaprein VIII (5) represents an isomer of pescaprein II (9) containing an n-dodecanoyl unit as the esterifying residue at position C-4 of the third rhamnose moiety and a 2-methylpropanoyl at C-2 of the second rhamnose. High-field NMR spectroscopy and FAB mass spectrometry were used to characterize all new isolated compounds.
Assuntos
Ácidos Graxos/isolamento & purificação , Glicosídeos/isolamento & purificação , Ipomoea/química , Plantas Medicinais/química , Resinas Vegetais/isolamento & purificação , Sequência de Carboidratos , Ácidos Graxos/química , Glicosídeos/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Resinas Vegetais/químicaRESUMO
This work evaluates the feasibility of reacting tannins isolated from Pinus radiata D. Don bark with epoxide resins of the diglycidyl and polyglycidyl ether type. To this end, gel times of aqueous tannin dispersions (40% w/w) with every one of nine selected resins (5% w/w), at previously established pH values (initial equal to 3.3, 4, 7 and 10), have been determined. Products of these reactions were analyzed by FT-IR spectroscopy, and the results were compared with those obtained from tannin-p-formaldehyde and (+)-catechin-p-formaldehyde systems, at the same pH values. Their mechanical properties were evaluated, by dynamic mechanical analysis, at two pH values (3.3 and 10). In general, it was concluded that tannin-epoxide resin systems behave similarly to tannin-paraformaldehyde systems, especially at basic pH values.
Assuntos
Compostos de Epóxi/metabolismo , Pinus/química , Casca de Planta/química , Resinas Vegetais/metabolismo , Taninos/metabolismo , Catequina/metabolismo , Compostos de Epóxi/química , Compostos de Epóxi/isolamento & purificação , Formaldeído/metabolismo , Concentração de Íons de Hidrogênio , Extratos Vegetais/química , Resinas Vegetais/química , Resinas Vegetais/isolamento & purificação , Espectroscopia de Infravermelho com Transformada de Fourier , Taninos/química , Taninos/isolamento & purificação , Temperatura , Fatores de TempoRESUMO
The floral resin of Tovomitopsis saldanhae (Guttiferae) is composed of poliisoprenylated benzophenone and the major constituent is 7-epi-nemorosone which has now been revised.
Assuntos
Benzofenonas/química , Benzofenonas/isolamento & purificação , Flores/química , Resinas Vegetais/química , Rosaceae/química , Conformação Molecular , Estrutura Molecular , Resinas Vegetais/isolamento & purificaçãoRESUMO
The resinous exudate of Baccharis grisebachii which is used to treat ulcers, burns, and skin sores in Argentina showed activity towards dermatophytes and bacteria. Two diterpenes, eight p-coumaric acid derivatives, and two flavones were isolated from the exudate and the structures elucidated by spectroscopic methods. 3-Prenyl-p-coumaric acid and 3,5-diprenyl-p-coumaric acid were active towards Epidermophyton floccosum and Trichophyton rubrum with MICs of 50 and 100-125 microg/ml, respectively. The diterpene labda-7,13E-dien-2beta,15-diol was active towards Epidermophyton floccosum and Trichophyton rubrum with MICs of 12.5 microg/ml while the MIC against Microsporum canis and Trichophyton mentagrophytes was 25 microg/ml. The diterpene was also active towards Microsporum gypseum with a MIC of 50 microg/ml, and showed inhibition in both Staphylococcus aureus (methicilline resistant and sensible strains) with MICs of 125 microg/ml. The results support the use of Baccharis grisebachii in Argentinian traditional medicine.
Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Baccharis , Resinas Vegetais/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antifúngicos/química , Antifúngicos/isolamento & purificação , Argentina , Bactérias/efeitos dos fármacos , Ácidos Cumáricos/química , Ácidos Cumáricos/isolamento & purificação , Ácidos Cumáricos/farmacologia , Diterpenos/química , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacocinética , Fungos/efeitos dos fármacos , Medicina Tradicional , Componentes Aéreos da Planta , Resinas Vegetais/química , Resinas Vegetais/isolamento & purificaçãoRESUMO
The antimicrobial properties of the resinous exudates from twigs and leaves of four Chilean species of Pseudognaphalium: P. viravira, P. robustum, P. heterotrichium and P. cheiranthifolium were tested against six gram negative bacteria and five gram positive bacteria. The extracts share similar antimicrobial activities against the gram positive bacteria. The antimicrobial activity correlated very well with the presence in the resinous exudates of ent-16-kauren-19-oic acid and to a lesser extent with the presence of ent-9(11),16-kauradien-19-oic. Introduction of an hydrophilic 3 beta-OH drastically reduced the antimicrobial activity of these compound. The activity was not correlated with the flavonoid content of those resinous exudates.
Assuntos
Diterpenos/farmacologia , Flavonoides/farmacologia , Extratos Vegetais/farmacologia , Bactérias/efeitos dos fármacos , Chile , Diterpenos/isolamento & purificação , Flavonoides/isolamento & purificação , Testes de Sensibilidade Microbiana , Resinas Vegetais/isolamento & purificação , Resinas Vegetais/farmacologiaRESUMO
One antimicrobial substance was obtained from the epicarp of the fruits of Paulownia fortunei and Paulownia tomentosa. Other parts of the fruits and leaves had no detectable antimicrobial activity. The substance was active in vitro for Staphylococcus aureus and Bacillus subtilis while it had lower activity for Saccharomyces carlsbergensis and the lowest was for Escherichia coli. The active material was extracted with organic solvents (ether, ethanol and acetone). The activity "in vitro" was demonstrated by the method of dilution in nutrient agar media. The active substance looked as a resin and was insoluble in water at neutral or acid pH. It was very soluble in strong alkaline pH solution.